2-Amino-4-(4-chloro­phen­yl)-4H-chromeno[8,7-b]pyridine-3-carbonitrile

The asymmetric unit of the title compound, C₁₉H₁₂ClN₃O, contains two mol­ecules with similar conformations. The 14 non-H atoms comprising the 4H-chromeno[8,7-b]pyridine residue are essentially coplanar (r.m.s. deviations = 0.037 and 0.042 Å for the two mol­ecules) and the main difference between them is seen in the twist about the bond linking the main residue to the attached chloro­benzene rings [dihedral angles = 79.01 (12) and 76.22 (11)° for the two mol­ecules]. Zigzag supra­molecular chains along the a-axis direction mediated by amino–pyridine N—H...N hydrogen bonds feature in the crystal packing; these are connected into a three-dimensional architecture by C—H...π inter­actions and Cl...Cl contacts [Cl...Cl = 3.3896 (14) Å].

3-Amino-1-(4-fluoro­phen­yl)-8-meth­oxy-1H-benzo[f]chromene-2-carbonitrile

The title compound, C₂₁H₁₅FN₂O₂, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052 Å), with the fluoro­benzene ring being almost perpendicular to this [dihedral angle = 85.30 (7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132 (2) Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å). In the crystal, inversion dimers are formed via pairs of amine–cyano N—H...N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C—H...N(cyano), C—H...π and π–π [inter­centroid distance = 3.6671 (10) Å] inter­actions.

3-Amino-1-(4-fluoro­phen­yl)-7-meth­oxy-1H-benzo[f]chromene-2-carbonitrile

In the title compound, C₂₁H₁₅FN₂O₂, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C₅ plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluoro­benzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supra­molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {...HNC₃N}₂ and eight-membered {...HNCO}₂ synthons. These are connected into a three-dimensional architecture by π–π [inter­centroid distance for centrosymmetrically related fluoro­benzene rings = 3.5181 (10) Å] and C—H...π inter­actions.

2-Amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile

In the title compound, C₂₁H₁₅BrN₂O₂, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446 Å). The bromo­benzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34 (13)°]. In the crystal, supra­molecular layers parallel to (101) are sustained by amine–cyano N—H...N and amine–meth­oxy N—H...O hydrogen bonds. The layers stack with inter­actions of the type (bromo­benzene)C—H...π(outer-C₆ ring of the fused-ring system) connecting them.

N′-[3-Cyano-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromen-2-yl]-N,N-dimethyl­methanimidamide

In the title compound, C₂₄H₂₀FN₃O₂, despite the 4H-pyran ring having a flattened half-chair conformation [the methine C atom lies 0.257 (3) Å above the plane of the remaining atoms with an r.m.s. deviation of 0.0295 Å], the 14 non-H atoms of the 4H-benzo[h]chromene residue are approximately coplanar (r.m.s. deviation = 0.081 Å). The benzene ring is nearly perpendicular to this plane [dihedral angle = 76.18 (10)°], but the planar (r.m.s. deviation = 0.033 Å) dimethyl­methanimidamide substituent is coplanar [dihedral angle = 1.96 (12)°]. In the crystal, centrosymmetric dimeric aggregates arise from C—H...N inter­actions, and these are connected into supra­molecular layers in the ab plane by C—H...π and π–π [inter­centroid (central C₆ ring)...(outer C₆ ring)ⁱ distance = 3.8564 (14) Å] inter­actions.

2-(4-Fluoro­benzyl­idene)propane­dinitrile: monoclinic polymorph

The title compound, C₁₀H₅FN₂, is a monoclinic (P2₁/c) polymorph of the previously reported triclinic (P-1) form [Anti­pin et al. (2003). J. Mol. Struct. 650, 1–20]. The 13 non-H atoms in the title polymorph are almost coplanar (r.m.s. deviation = 0.020 Å); a small twist between the fluoro­benzene and dinitrile groups [C—C—C—C torsion angle = 175.49 (16)°] is evident in the triclinic polymorph. In the crystal, C—H...N inter­actions lead to supra­molecular layers parallel to (-101); these are connected by C—F...π inter­actions.

3,3-Bis(4-bromo­phenyl­sulfan­yl)-1-methyl­piperidin-2-one

In the title compound, C₁₈H₁₇Br₂NOS₂, the conformation of the piperidin-2-one ring is based on a half-chair with the methyl­ene C atom diagonally opposite the N atom being 0.649 (3) Å above the plane of the remaining five atoms (r.m.s. deviation = 0.1205 Å). The S atoms occupy axial and bis­ectional positions, and the dihedral angle between the benzene rings of 59.95 (11)° indicates a splayed disposition. Helical supra­molecular chains along the b axis sustained by C—H...O inter­actions is the major feature of the crystal packing. The chains are connected into a three-dimensional architecture by C—H...Br and C—H...π inter­actions.

2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

In the title compound, C₂₄H₁₇ClFN₃S, the pyrazole ring is almost planar (r.m.s. deviation = 0.030 Å). With the exception of the methine-bound benzene ring, which forms a dihedral angle of 85.77 (13)° with the pyrazole ring, the remaining non-C atoms lie in an approximate plane (r.m.s. deviation = 0.084 Å) so that overall the mol­ecule has a T-shape. In the crystal, centrosymmetrically related mol­ecules are connected via π–π inter­actions between pyrazole rings [centroid–centroid distance = 3.5370 (15) Å] and these stack along the a axis with no specific inter­actions between them.

5-Methyl-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-yl­idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

In the title compound, C₁₈H₁₄N₆O₂, the benzene ring is slightly twisted out of the plane of the 1,2,3-triazole ring (r.m.s. deviation = 0.010 Å), forming a dihedral angle of 6.20 (13)°. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.032 Å). The near coplanarity in the central residue is consolidated by an intra­molecular bifurcated N—H...(O,N) hydrogen bond. The conformation about the N=C bond is Z. In the crystal, supra­molecular chains along [101] are sustained by N—H...O hydrogen bonds and C—H...O inter­actions. These are consolidated into a three-dimensional architecture by C—H...π and π–π inter­actions; the latter occur between centrosymmetrically related 1,2,3-triazole rings [centroid–centroid distance = 3.6056 (14) Å].

4-[5-(4-Fluoro­phen­yl)-1-(4-phenyl-1,3-thia­zol-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]-5-methyl-1-(4-methyl­phenyl)-1H-1,2,3-triazole

In the title compound, C₂₈H₂₃FN₆S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluoro­benzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the mol­ecule has a T-shape. In the crystal, mol­ecules are consolidated into a three-dimensional architecture by C—H...F (involving a bifurcated F atom), C—H...S and C—H...π inter­actions.

5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio­amide

In the title compound, C₂₆H₂₃FN₆S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thio­urea group is close to being coplanar with the pyrazole N atoms [N—N—C—S torsion angle = 176.78 (15)°], which allows for an intra­molecular N—H...N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N—C—C—N = −172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluoro­benzene ring [N—C—C—C = −18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supra­molecular chains aligned along [40,10] are consolidated by π–π inter­actions between the triazole and phenyl rings [centroid–centroid distance = 3.7053 (13) Å].